Oral care compositions comprising dicarboxy functionalized polyorganosiloxanes

a functionalized polyorganosiloxanes and oral care technology, applied in the field of oral care compositions comprising dicarboxy functionalized polyorganosiloxanes, can solve the problems of inability to achieve the effect of coating the teeth with pdms polymers, constant source of irritation of gingiva, and undesirable appearance to the outside, so as to prevent, reduce or remove plaque, calculus and surface deposited stains, and prolong retention

Inactive Publication Date: 2006-04-11
THE PROCTER & GAMBLE COMPANY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

[0013]The present invention provides oral compositions for use in cleaning and whitening of natural teeth and dental prosthesis and for preventing, reducing or removing plaque, calculus and surface deposited stains on teeth, the compositions comprising at least about 0.1% by weight of a carboxy functionalized siloxane polymer in a formulation that effectively deposits the polymer to teeth and other oral surfaces, forming a substantive coating having prolonged retention thereon. The present polymers comprise a hydrophobic siloxane backbone having pendant moieties containing carboxy groups, and have the ability to deposit onto polar surfaces, i.e., having cationic sites. The compositions may be aqueous or essentially non-aqueous based and may further comprise one or more oral care actives such as teeth whitening agents including bleaches and color modifying agents, antimicrobials, enzymes, fluoride, desensitizing agents, and flavors. This invention further relates to methods of cleaning and whitening natural teeth and dental prosthesis; preventing, reducing or removing plaque, caries, tartar, and surface deposited tooth stains; and providing shine, smoothness and positive tooth feel benefits by administering the present compositions.

Problems solved by technology

However, PDMS polymers have not generally been used successfully for coating the teeth because of poor adhesion and retention of the PDMS on tooth surfaces.
Either the enamel or pellicle or both can be discolored or stained and present to the outside an undesirable appearance.
In addition to being unsightly and undesirable from an aesthetic standpoint, the mature calculus deposits are constant sources of irritation of the gingiva.
The failure to retard or stop the proliferation of plaque and calculus is detrimental to oral health.
Plaque and calculus formation may lead to dental caries, gingival inflammation, periodontal disease, and ultimately tooth loss.
Additionally, calculus and plaque along with behavioral and environmental factors lead to formation of dental stains, significantly affecting the aesthetic appearance of teeth.

Method used

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  • Oral care compositions comprising dicarboxy functionalized polyorganosiloxanes
  • Oral care compositions comprising dicarboxy functionalized polyorganosiloxanes

Examples

Experimental program
Comparison scheme
Effect test

example 1

Preparation of a Dicarboxy Functionalized Polydimethylsiloxane Having Pendant —(CH2)3—CH(COOH)—CH2COOH Groups

[0116]93.7 g (i.e., 0.67 mol) of allyl succinic anhydride, 52 g of toluene and 1.01 g of a Kardtedt catalyst solution (0.1% of Pt in hexamethyldisiloxane) are added into a 500 ml reactor. The reaction mass is heated at 90° C.; 120 g (i.e., 0.45 mol of SiH) of a polydimethylhydrogenosiloxane having the formula

Me3SiO(SiMe2O)9(SiMeHO)4SiMe3

and containing 3.75 mol of SiH / kg, are added over 3 hours. The SiH amount (determined by gazometry) transformed at the end of the addition is of 96.1%; it is of 100% 2 hours after the end of the addition. The volatiles are eliminated by evaporation under vacuum (3 mbar) over 10 hours at 150° C. 15 g of demineralized water are then added in order to hydrolyze the succinic anhydride functions. The hydrolysis reaction is followed by infra-red analysis (acid band at 1714 cm−1, anhydride band at 1863 and 1782 cm−1). When the hydrolysis reaction is ...

example 2

Preparation of a Dicarboxy Functionalized Polydimethylsiloxane Having Pendant —(CH2)3—CH(COOH)—CH2COOH Groups

[0118]49.8 g (i.e., 0.36 mol) of allyl succinic anhydride, 44 g of toluene and 1.139 g of a Kardtedt catalyst solution (0.1% of Pt in hexamethyldisiloxane) are added into a 500 ml reactor. The reaction mass is heated at 90° C.; 150.3 g (i.e., 0.266 mol of SiH) of a polydimethylhydrogenosiloxane having the formula

Me3SiO(SiMe2O)100(SiMeHO)15SiMe3

and containing 1.77 mol of SiH / kg, are added over 1 hour. The SiH amount (determined by gazometry) transformed at the end of the addition is of 86%; it is of 100% 16 hours after the end of the addition. The volatiles are eliminated by evaporation under vacuum (6 mbar) over 10 hours at 150° C. 101 g of toluene are added; the reaction mass is filtered. 6.7 g of demineralized water are then added in order to hydrolyze the succinic anhydride functions. The hydrolysis reaction is followed by infrared analysis (acid band at 1714 cm−1, anhydri...

example 3

Retention of Functionalized Siloxane Polymers Applied as a 1% Solution on Polished Bovine Enamel Surfaces

[0120]The deposition and retention of dicarboxy functionalized siloxane polymers according to the present invention applied as a 1% solution on polished bovine enamel surfaces are compared with other siloxane polymers containing other functional groups. Solutions of the different siloxane polymers were prepared at 1% concentration in MIBK (methyl isobutyl ketone). Six □l of each solution was applied directly to clean, polished bovine enamel specimens set in resin, having approximately 1 cm2 surface area. The solvent was allowed to evaporate under ambient conditions and an initial water contact angle (WCA) was measured using a Kruss DSA-10 system. The enamel specimens were then soaked in ultra pure water for 5 minutes, and after allowing to air dry the water contact angle was re-measured. Then, the specimens were brushed on a brushing machine (V-8 crossover with an Oral-B flat hea...

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Abstract

Disclosed are compositions and methods for treating and modifying surfaces and for enhancing delivery of active agents to surfaces treated with the compositions, which comprise siloxane polymers functionalized with pendant moieties comprising anionic groups, specifically carboxylic acid groups. When applied to a suitable surface, the present composition comprising the carboxy functionalized siloxane polymers forms a substantially hydrophobic coating on the treated surface. These polymers effectively deposit on surfaces that have cationic sites, which are capable of forming bonds or linkages with the anionic groups of the polymer. The treated surface becomes hydrophobic due to the deposition of the carboxy functionalized siloxane polymer, which then imparts a variety of end use benefits to that surface such as ease of cleaning, stain removal and prevention, whitening, etc. The carboxy functionalized siloxane polymer further acts as a carrier to deposit active agents onto the surface and to improve retention and efficacy of said actives on the treated surface. The present compositions are useful in a variety of applications including oral care, hair and skin care, personal care, cosmetics, and fabric and hard surface cleaning and conditioning. Examples are oral compositions for use in cleaning and whitening of natural teeth and dental prosthesis; for preventing, reducing or removing plaque, calculus and surface deposited stains on teeth; and for providing shine, smoothness and positive feel benefits to teeth, the compositions comprising at least about 0.1% by weight of a dicarboxy functionalized siloxane polymer in a formulation that effectively deposits the polymer to teeth and other oral surfaces.

Description

CROSS REFERENCE TO RELATED APPLICATIONS[0001]This application claims the benefit of U.S. Provisional Application No. 60 / 378,994, filed May 9, 2002.FIELD OF THE INVENTION[0002]This invention provides compositions and methods for treating and modifying surfaces and for enhancing delivery of active agents to surfaces treated with the compositions which comprise siloxane polymers functionalized with pendant moieties comprising anionic groups, specifically carboxy groups. When applied to a suitable surface, the present composition comprising the carboxy functionalized siloxane polymers forms a substantially hydrophobic coating on the treated surface. These polymers effectively deposit on surfaces that have cationic sites, which are capable of forming bonds or linkages with the anionic groups of the polymer. The treated surface becomes hydrophobic due to the deposition of the carboxy functionalized siloxane polymer, which then imparts a variety of end use benefits to that surface such as ...

Claims

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Application Information

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Patent Type & Authority Patents(United States)
IPC IPC(8): A61K8/00A61K8/365A61K8/22A61K8/89A61K8/893A61K8/896A61Q11/00
CPCA61Q11/00A61K8/893A61K8/72A61K8/896
Inventor MAJETI, SATYANARAYANARENO, ELIZABETH ANN BROWNKOVACS, STEPHEN ANDRASGLANDORF, WILLIAM MICHAELOLIER, PHILIPPE
Owner THE PROCTER & GAMBLE COMPANY
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